An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes

Enantioselective quaternary carbon construction in the assembly of cyclopentenones employing a Rh(II)-catalyzed, formal [4+1]-cycloaddition is described. A Rh(2)(S-TCPTTL)(4)-catalyzed cyclopropanation of a vinyl ketene with a disubstituted diazo compound initiates a stereoretentive, accelerated rin...

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Detalles Bibliográficos
Autores principales: Rodriguez, Kevin X., Pilato, Tara C., Ashfeld, Brandon L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5931190/
https://www.ncbi.nlm.nih.gov/pubmed/29844895
http://dx.doi.org/10.1039/c8sc00020d
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author Rodriguez, Kevin X.
Pilato, Tara C.
Ashfeld, Brandon L.
author_facet Rodriguez, Kevin X.
Pilato, Tara C.
Ashfeld, Brandon L.
author_sort Rodriguez, Kevin X.
collection PubMed
description Enantioselective quaternary carbon construction in the assembly of cyclopentenones employing a Rh(II)-catalyzed, formal [4+1]-cycloaddition is described. A Rh(2)(S-TCPTTL)(4)-catalyzed cyclopropanation of a vinyl ketene with a disubstituted diazo compound initiates a stereoretentive, accelerated ring expansion to provide the cycloadduct in good to excellent yields and enantioselectivity.
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spelling pubmed-59311902018-05-29 An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes Rodriguez, Kevin X. Pilato, Tara C. Ashfeld, Brandon L. Chem Sci Chemistry Enantioselective quaternary carbon construction in the assembly of cyclopentenones employing a Rh(II)-catalyzed, formal [4+1]-cycloaddition is described. A Rh(2)(S-TCPTTL)(4)-catalyzed cyclopropanation of a vinyl ketene with a disubstituted diazo compound initiates a stereoretentive, accelerated ring expansion to provide the cycloadduct in good to excellent yields and enantioselectivity. Royal Society of Chemistry 2018-02-19 /pmc/articles/PMC5931190/ /pubmed/29844895 http://dx.doi.org/10.1039/c8sc00020d Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Rodriguez, Kevin X.
Pilato, Tara C.
Ashfeld, Brandon L.
An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes
title An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes
title_full An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes
title_fullStr An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes
title_full_unstemmed An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes
title_short An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes
title_sort unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective rh(ii)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5931190/
https://www.ncbi.nlm.nih.gov/pubmed/29844895
http://dx.doi.org/10.1039/c8sc00020d
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